Journal of Al-Nahrain University Vol.18 (1), March, 2015, pp.28-38 Science

28

Synthesis, Characterization and Theoretical Study of Some Mixed-ligand

Complexes of 2-Quinoline Carboxylic Acid and 4,4⁄ -dimethyl,2,2⁄-Bipyridyl with

Some Transition Metal Ions

Mahasin Alias , Sahar Ismael and Souad Abd Mousa

Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad-Iraq.

Abstract New mixed ligand complexes have been prepared by the reaction of Quinoline- 2-Carboxylic

Acid (HL1) and 4,4⁄ -dimethyl,2,2⁄-Bipyridyl (L2) with Co(II),Ni(II) Cu(II), Zn(II), Pd(II) and

Au(III) ions. The newly prepared complexes were isolated and characterized by (FT-IR) and (UV-

Vis) spectroscopy, elemental analysis, flame atomic absorption technique, thermo gravimetric

analysis, in addition to magnetic susceptibility and conductivity measurements. A theoretical

treatment of these ligands and prepared complexes in gas phase were studied using Hyper chem.8

program, moreover, ligands in gas phase also have been studied using Gaussian program

(GaussView Currently Available Versions (5.0.9) along with Gaussian 09 which is the latest in the

Gaussian series of programs).

Keywords: Quinoline-2-Carboxylic Acid, 4,4⁄-dimethyl,2,2⁄-Bipyridyl, Hyperchem.8,spectroscopy,

Theoretical treatment, Gaussian program.

1.Introduction Quinoline carboxylic acids and their

analogues show a wide variety of medicinal

properties including antitumor [1], antiviral

[2], and estrogenic activity [3]. Recent

demonstrations reveal that quinoline-2-

carboxylic acid can be used as potential

anticancer agents [4], and a biological

compound involved in the metabolism of

tryptophan. It is a strong chelator that provides

the donor set similar to that responsible for

binding metal ion in pyrroloquinilnequinone

cofactor of quinoprotein family [5]. 2,2/-

Bipyridine is known to form stable chelate

complexes even with low valent transition

metal ions [6]. Today, it is even one of the

most widely used chelate systems in

coordination chemistry and in recent years has

also become a very popular ligand in

supramolecular and macromolecular chemistry

[7]. A quinoline-2-carboxylic acid and co-

ligand 4,4⁄-dimethyl-2,2⁄-Bipyridyl did not

receive any attention in spite of well-defined

applications of both molecules. Hence, it was

thought to explore the study, synthesis and

characterization of some new complexes of

quinoline-2-carboxylic acid and co- ligand

4,4⁄dimethyl-2,2⁄-Bipyridyl as mixed ligand

complexes.

2. Experimental 2.1. Physical Measurements and Analysis

Melting point apparatus of Gallen Kamp

M.F.B-60 was used to measure melting points

of all compounds.FT-IR spectra were recorded

as CsI discs using FT-IR3800 Shimadzu in the

range of (4000-200 cm-1). Electronic spectra

were obtained using UV-1650PC

Spectrophotometer at room temperature in

DMF solvent. Conductivity was measured by

capacitor analyzer in DMF solution (10-3 M) at

room temperature using (WTW)

Conductometer. Elemental analysis was

performed by using EM-017mth instrument.

Magnetic susceptibility measurements

were obtained at 25 οC Magnetic Susceptibility

Balance of Johnson matty catalytic system

division, England. The metal percent of all the

complexes were determined by using GBS-

933 Flam plus Atomic Absorption

Spectrophotometer. The thermal analysis of all

the prepared complexes have been carried out

by 4000 Perkin–Elmer thermal analyzer

maintained at a 20.00 oC min-1 heating rate.

2.2. Synthesis of Metal complexes A solution containing the primary ligand

Quinoline-2-Carboxylic acid in 10 ml of

absolute ethanol, and the secondary ligand

4,4/-dimethyl-2,2/- Bipyridyl in 5 ml of

absolute ethanol were added to a 5 ml warm

Mahasin Alias

29

absolute ethanol of metal salts

Co(NO3)2.6H2O,Ni(NO3)2.6H2O,Cu(NO3)2.3H

2O, (CH3COO)2Zn.2H2O ,PdCl2 ,and

HAuCl4.H2O in molar ratio 1:1:1respectively.

The mixture was heated and refluxed with

stirring for (3-4) hrs. The colored precipitates

were filtered, washed several times with

ethanol, and finally recrystalized by ether-

ethanol mixture then dried using desiccators.

3. Results and Discussion Some physical properties and data of the

ligands (HL1) and (L2) with their metal

complexes are given in Table (1). The molar

conductivity in DMF solvent indicates the

electrolyte behavior of all complexes except

Zn (II) complex [8].

Table (1)

Some physical and analytical data for the ligands and their metal complexes.

Comp. Color M.P OC Yield% M.Wt

g.mol-1

Elemental analysis%

Found (Calc.)

C H N M

C10H7NO2 (HL1) White 154-156 ---- 173.17 ---- ---- ---- ----

C12H12N2 (L2) White 172-174 ---- 184.64 ---- ---- ---- ----

[CoL1L2] NO3.2H2O Greenish

blue 96-98 70.96 513.67

51.963

(51.40)

5.075

(4.28)

10.131

(10.90)

12.06

(11.46)

[NiHL1L2(H2O)2](NO3)2.H2O Pale

green 144-146 77.41 594.46

45.246

(44.41)

3.469

(4.21)

10.911

(11.77)

10.54

(9.87)

[CuHL1L2(H2O)2] (NO3)2 Olive 182-184 86.75 581.34 44.630

(45.41)

3.967

(3.95)

11.530

(12.04)

11.13

(10.93)

[ZnL1L2(OAC)H2O] Off

White 116-118 70.37 499.13

56.983

(57.70)

5.183

(4.60)

7.974

(8.41)

12.51

(13.10)

[PdL1L2] Cl.1/2 H2O Pale

brown 186-188 90.26 507.63

53.000

(52.00)

3.180

(3.54)

7.943

(8.27)

21.07

(20.98)

[AuL1L2] Cl2.H2O Brown 104-106 84.68 642.57 40.514

(41.08)

2.828

(3.11)

6.210

(6.53)

30.26

(30.66)

3.1. Infrared Spectra Studies Table (2) shows tentative assignments of

the IR peaks for the free quinoline -2-

carboxylic acid and some metals together with

the co-ligand 4,4/-dimethyl-2,2/ Bipyridyl. The

(HL1) may coordinate with metal ions through

monodentate, bidentate chelating and bridging

according to Nakamoto and Deacon & Phillips

[9].The infrared spectrum of the solid state

2-quinaldic acid indicates that it’s exists in two

tautomeric forms at the same time, as a neutral

molecule (quinoline-2-carboxylic acid) and

as a zwitter ion (quinolinium-2-carboxylate)

[10].IR spectrum of the ligand shows a typical

broad band in the range (3417-2534) cm-1 with

its maximum at (2939) cm-1 which refers to

stretching frequency of ν (O-H) of carboxylic

acid [9b].This can still be observed in the IR

spectrum of nickel and copper complexes, this

confirmed the incomplete deprotonation of

ligand in these complexes [11].On the other

hand, the absence of absorption bands in this

region in IR spectra for all complexes

confirmed the complete deprotonation of the

ligand in these complexes [12]. Further

confirmation comes from the absence of

C-O-H bending peak for COOH group at

908 cm-1 [13]. The difference of the

value between the asymmetric and

symmetric stretching of COO- frequencies

(Δν = νsymCOO- - νasym COO-) of all complexes

have been compared in order to predict the

coordination mode of metal ions with

quinoline-2-carboxylic acid as shown in

Table (2). The Δν values, for each prepared

complexes, indicates the monodentate

coordination of the carboxylate group. The

bending of δ (C=N) in all complexes shifted

Journal of Al-Nahrain University Vol.18 (1), March, 2015, pp.28-38 Science

30

and appeared at the range (408-393) cm-1 with

its maximum at (405) cm-1 [14].indicates that

the nitrogen atom of quinoline-2-carboxylic

acid also had coordinated with metal ions.

Furthermore, new bands attributed to ν (M-O)

and ν (M-N) which appeared at (570-520) cm-1

and (420-489)cm-1 respectively in all

complexes also confirmed L1 had coordinated

with the metal ions through oxygen atom of

carboxylate group and nitrogen atom [9b]. The

coordination of 4,4/-dimethyl-2,2/ Bipyridyl is

indicated by the positive shift of ν(C=C) and

ν(C=N) ring streching frequencies and the

presence of their deformation modes at 1168

and 1936cm-1. The position of the bands which

was found in the spectrum of 4,4/-dimethyl-

2,2/ Bipyridyl has been completely changed in

the spectra of the complexes where it is used

as co-ligand and new bands appeared at

~1560-1590 cm-1 confirming the coordination

nature of this ligand, the 424 cm-1 band of 4,4/-

dimethyl-2,2/ Bipyridyl (C-C out of plane

bending) shifts to higher frequency and splits

into two components in the complexes which

again confirms the coordination of this ligand

through two nitrogen atoms [10]. An

additional band in the range (260-270) cm-1

which has been observed in all complexes

indicates that the nitrogen atoms of the

co-ligand coordinates with metal ion [15]. The

presence of water molecules causes the

appearance of broad O-H stretching bands

in the region of 3473-3417 cm-1 in most

IR spectra of the complexes [16].

Table (2)

Main FTIR bands in (cm -1) observed in the spectra of metal ions mixed ligands complexes.

Comp. νasy.

COO-

νsym.

COO νC=O νC=N+νC=C

ν

M-N ν

M-O

ν

M-N

(Bipy)

Others

C10H7NO2 (HL1) 1580 1390 1697 1604,1535,

1508, 1473 ---- ---- ---- ----

C12H12N2 (L2) ---- ---- ---- 1604,1519,

1481, 1450 ---- ---- ---- ----

[CoL1L2] NO3.2H2O 1592 1384 ---- 1612,1562,

1512, 1462 443 570 262

νOH=3441

δH2O=848.6

NO3=1384,1176,

964

[NiHL1L2(H2O)2](NO3)2.H2O 1595 1394 1693 1612,1560,

1512, 1465 489 528 270

νOH=3402

δH2O=856

NO3=1394,1176,

968

[CuHL1L2(H2O)2] (NO3)2 1598 1381 1693 1612,1562,

1512, 1465 489 524 262

νOH=3348.7

δH2O=856.3

NO3=1381,1172,

948

[ZnL1L2(OAC)H2O] 1594 1388 1697 1612,1566,

1516, 1465 420 528 266

δH2O=852

OAC=1728

[PdL1L2] Cl.1/2 H2O 1572 1365 ---- 1600,1528,

1516,1465 455 528 262 νOH=3348.4

[AuL1L2] Cl2.H2O 1575 1365 ---- 1604,1527,

1506, 1454 455 536 262 νOH=3448

3.2. Magnetic Moment Study

The magnetic moment (μeff) for the cobalt

(II) complex (d7) has been estimated to be

(4.56) B.M. This higher value of (μeff) in this

complex may be due to the contribution of

spin orbital coupling [17]. In nickel (II)

complex, it was recorded at (3.11) B.M. [18],

while the (μeff) of the cupper (II) complex is

(2.11) B.M [19]. This value lies within the

expected value for one electron. On the other

hand, zinc (II), palladium (II), and gold (III)

complexes are diamagnetic Table (3).

3.3. The Electronic Spectra

3.3.1. Electronic Spectra of Ligands

The electronic spectrum of H L1 exhibits

four main bands appeared at 45045 cm-1 ,

41666 cm-1, 34843 cm-1, and a shoulder band

at 30487 cm-1 due to (π→π*), (n→π*),

(n→π*) and (n→π*) transitions respectively

Mahasin Alias

31

[20]. While the Electronic spectrum of

L2 exhibits two main bands: the first one

appeared at 41152 cm-1 due to interaligand

(π→π*) transition, the second absorption

appeared at 33670 cm -1 arises from (n→π*)

transition that may be located on nitrogen

atom of –N=C-. A comparative look of

electronic absorption spectral data of the

ligands and their complexes indicates that

n→π* and π→π* transitions of the ligands has

shifted to higher frequencies [20], Table (3).

3.3.2 Electronic Spectra of [CoL1L2]

NO3.2H2O Complex

The greenish-blue complex showed three

bands at 16583, 16447, and 14947 cm -1 which

assigned to 4A2→4T1p ν3 transition. This

transition is known to be triplet in the divalent

cobalt of tetrahedral geometry. This splitting

is due to spin orbital coupling [21]; therefore,

ν3 has been calculated as the average of these

three bands.While ν1 (4A2→4T2 ) and ν2

(4A2→4T1) could not be seen since which

expected to appear in the range out of scale, so

the second transition (ν2) calculated

theoretically and it has been estimated to be

(5393) cm-1, while first transition (ν1)

calculated from infrared spectrum and found

to be (3441) cm-1; moreover, B/, Dq, and β

were calculated and the low value of β

indicates that the bond is covalent. These

parameters are accepted for cobalt (II)

tetrahedral complexes [21], Table (3).

3.3.3 Electronic Spectra of

[NiHL1L2(H2O)2](NO3)2.H2O Complex

The electronic spectrum of nickel (II)

complex showed three bands at 9803, 14662,

and 30211 cm-1 which corresponding to 3A2g→3T2g, 3A2g→3T1g, and 3A2g→3T1g(p)

respectively. The spectrum also shows a band

at 13333 cm-1 corresponds to 3A2g→1Eg

which refers to forbidden transition. These

bands indicate an octahedral geometry around

Ni (II) ion [22]. The absence of the frequency

at (20000) cm-1 proves that the prepared

complex is not square planer [23a].

Nephelauxetic factor β and Racah parameter

B/ were calculated by fitting the ratio ν3/ν2

from Tanabe-Sugano diagram for d8 system

Table (3).

By fitting the ratio of frequencies (ν2/ν1)

which equals to 1.5 indicates that the complex

has distorted octahedral geometry [23b],

comparable with the value of a regular

geometry which equals to 1.6[24]. The

formula is further confirmed to be ionic by

conductivity measurements. From these

results and other analyses, an octahedral

geometry around Ni (II) ion can be proposed

3.3.4. Electronic Spectra of

[CuHL1L2(H2O)2] (NO3)2Complex

Electronic spectrum of Cu (II) complex

shows a broad absorption band at 11695 cm-1

which refers to electronic transition 2B1g →2A1g. The second band at 26666 cm-1

which assigned to 2B1g →2Eg transition [25],

as well as another band at 28653cm-1 which

corresponds to charge transfer from the donor

atoms of ligands to cupper (II) ion, Table (3).

3.3.5. Electronic Spectra of

[ZnL1L2(OAC)H2O]Complex

Since the UV–Visible spectra of d10 ion do

not furnish a lot of information, therefore,

some shifting and change in the shape of the

bands were compared with those of ligands

[26]. The prepared off white Zn(II) complex

shows two bands at 41841 and 33444 cm-1, as

well as a shoulder at 30864 cm-1.

3.3.6 Electronic Spectra of [PdL1L2] Cl.1/2

H2O Complex

The spectrum of Pd(II) complex shows

band at 21645 and 28011 cm-1 which are

assigned to 1A1g→1B1g and 1A1g→1E1g

transitions [27], while the band appearing at

31250 cm-1 is correspond to L→PdCT

transition [23b], Table (3), the results are in

fairly good agreement with literatures which

suggest that Pd(II) complex has square planer

environments of ligands [28].

3.3.7 Electronic Spectra of [AuL1L2]

Cl2.H2O Complex

The electronic spectrum of this complex

Table (3) shows three bands at 26666,

29850 cm-1 which refers to 1A1g→1B1g and 1A1g→1Eg transition respectively, and the

third band appeared at 30769 cm-1 due to

charge transfer in square planner geometry

[29].

Journal of Al-Nahrain University Vol.18 (1), March, 2015, pp.28-38 Science

32

Table (3)

Electronic spectra, conductance in DMF solvent and magnetic moment (B.M) for

ligands and their metal complex.

Comp. C10H7NO2

(HL1)

C12H12N2

(L2)

[CoL1L2]

NO3.2H2O

[NiHL1L2(H2O)2]

(NO3)2.H2O

[CuHL1L2

H2O)2]

(NO3)2

[ZnL1L2

(OAC)H2O]

[PdL1L2]

Cl.1/2 H2O

[AuL1L2]

Cl2.H2O

Absorption

30487(sh)

34843

41666

45045

33670

41152

3441

5393(cal.)

15992(av.)

13333

9803

14602

30211

11695

26666

28653

30846 (sh)

33444

41841

21645

28011

31250

26666

29850

30769

Assignment

n→π*

n→π*

n→π*

π→π*

n→π*

π→π*

4A2→4T2

4A2→4T1

4A2→4T1(P)

3A2g→1Eg

3A2g→3T2g

3A2g→3T1g

3A2g→3T1g

2B1g→2A1g

2B1g →2Eg

L→CuCT

ILCT

ILCT

ILCT

1A1g→1B1g

1A1g→1Eg

L→PdCT

1A2g→1B1g

1A2g→1Eg

L→AuCT

Bо ---- ---- 971 1035 ---- ---- ---- ----

B/ ---- ---- 737.5 917.6 ---- ---- ---- ----

β ----- ---- 0.75 0.88 ---- ---- ---- ----

Dq/B/ ----- ---- 0.47 1.1 ---- ---- ---- ----

10Dq ---- ---- 3460 9900 ---- ---- ---- ----

15 B/ ---- ---- 11062 989.9 ---- ---- ---- ----

𝜇eff ---- ---- 4.56 3.11 2.11 0.00 0.00 0.00

𝜇scm-1 ---- ---- 76.6 72.7 72.2 16.6 73.4 52.6

Suggested

Structure ---- ---- T.d O.h O.h O.h

Sq.

Planer

Sq.

Planer

ILCT: Internal ligand charge transfer.

3.4 Thermal Analysis Thermal analyses were done to confirm the

presence of water molecules as suggested in

the new prepared complexes by following the

degradation steps in TG curves and the

obtained results has been listed in Table (4).

Table (4)

Thermal analytical data of the water molecule for the newly prepared complexes.

Comp Weight loss

found (Calc.)%

Temp range in

TG (οC )

[CoL1L2] NO3.2H2O 6.51(7.00) 118.93-220.71

[NiHL1L2(H2O)2](NO3)2.H2O 8.58(9.08) 129.65-170.22

[CuHL1L2(H2O)2] (NO3)2 4.71(5.19) 122.15-192.62

[ZnL1L2(OAC)H2O] 2.93(3.63) 282.33

[PdL1L2] Cl.1/2 H2O 0.98(1.07) 72.60-225.86

[AuL1L2] Cl2.H2O 2.92(2.80) 74.90—220.10

Mahasin Alias

33

3.5 Suggested Structures of new Complexes

4. Theoretical Studies

In this work, Hyperchem.8 program has

been used to calculate The heat of formation

(ΔHоf), binding energy (ΔEb) and dipole

moment (µ) for the free ligands and their metal

complexes using semi-empirical (ZINDO/I,

PM3) and molecular mechanics (AMBER )

methods at 298 K. It was found that the

complexes are more stable than their ligands

Table (5); Furthermore, the electrostatic

potential for free ligands was calculated to

investigate the reactive site of the molecules,

PM3 was used to evaluate the vibrational

spectra of free ligands. It has been found that

these obtained frequencies agree well with

experimental results; in addition, the

calculation helped to assign unambiguously

the most diagnostic bands Table (6).

Electronic spectra measurements for the

ligands were calculated theoretically by using

ZINDO/S method and comparing it with the

experimental results. It was found that there

was a close agreement between the theoretical

calculations and experimental results

Table (7). While Gaussian program semi-

empirical (PM3) method was used to calculate

the geometry optimization, dipole moment (μ)

and total energy as shown in Table (8).

Electrostatic potential, ELUMO and EHOMO was

obtained also; evaluate the vibrational spectra

of free ligands, and these obtained frequencies

agree well with experimental results as shown

in Table (9). Electronic spectra measurements

for the ligands were calculated theoretically by

using the job type: Single point energy (SP)

along with ZINDO method and also the job

type Frequency (Freq) used along with CIS

method (3-21G) and compared both methods

with the experimental results as shown in

Table (10). It was found that there was a close

agreement between the theoretical and

experimental results.

Journal of Al-Nahrain University Vol.18 (1), March, 2015, pp.28-38 Science

34

Table (5)

Conformation energetic in (Kcal.mol-1) and dipole moment (in Debye) for ligands and

their metal complexes using hyperchem-8 program.

Compound PM3 ZINDO/1 AMBER

ΔHоf ΔEb µ ΔHо

f ΔEb µ ΔHоf=ΔEb

C10H7NO2 (HL1) -39.8326 -2345.56 3.027 -4515.74 -6821.47 3.324 ----

C12H12N2 (L2) 329.69 -2259.59 4.589 -4860.72 -7450.01 5.209 ----

{CoL1L2]NO3.2H2O ---- ---- ---- -10216.87 -15474.80 13.84 ----

[NiHL1L2(H2O)2](NO3

)2. H2O ---- ---- ---- -10993.76 -16631.72 8.291 ----

[CuHL1L2(H2O)2]

(NO3)2 ---- ---- ---- -11412.33 -17028.19 12.13 ----

[ZnL1L2(OAC)H2O] ---- ---- ---- -12836.02 -18803.69 10.78 ----

[PdL1L2] Cl.1/2 H2O ---- ---- ---- ---- ---- ---- 44.01

[AuL1L2] Cl2.H2O ---- ---- ---- ---- ---- ---- 48.47

Table (6)

Comparison of experimental and theoretical main vibration frequencies for Qinoline-2-

carboxylic acid (HL1) and 4,4⁄-dimethyl -2,2⁄-bipyridyl(L2)using hyperchem-8program

Symb. ν(C=O) ν(C=N+C=C) δ(C-O) ν(O-H)

HL1

1980.78

1697.36*

(16.69)

1631.59

1604*

(1.68)

1394.36

1261.45 *

(10.54)

3852.17

2939 *

(4.47)

Symb. ν(C=N+C=C) ν(C-H)aliph. ν(C-H)arom. δ(C-N)

L2

1780.43

1604.77*

(10.94)

3170.58

2981.95*

(2.99)

3035.50

3078.39*

(0.033)

1233.03

1273.02*

(-3.14)

(*) Experimental Frequency Error .

Table (7)

Comparison of experimental and theoretical electronic transition for ligands from ZINDO/S

calculation and Experiment method using hyper chem-8 program.

Symbols Transition Experimental Theoretical(ZINDO/S)

HL1

n→π

n→π*

n→π*

π→π*

328sh

287

240

222

306

279.4

229

214

L2

n→π*

π→π*

n→π*

π →π*

297

243

-------

-------

274.55

--------

237.02

195.0

Mahasin Alias

35

Table (8)

Conformation energetic in (Kcal.mol-1) and dipole moment (in Debye) for ligands

(HL1,L2) using Gaussian program.

Compound Total energy µ

HL1 -32.44762449 3.3846

L2 45.4167809 3.4377

Table (9)

Comparison of experimental and theoretical vibration frequencies for Qinoline-2-carboxylic acid

(HL1) 4,4⁄-dimethyl-2,2⁄-bipyridyl (L2)using Gaussian programs.

Symb. ν(C=O) ν(C=N+C=C) δ(C-O) ν(O-H)

HL1

2065.71

1697.36*

(17.83)

1628.07

1604*

(1.47)

1282.41

1261.45 *

(1.63)

3239.37

2939 *

(9.27)

Symb. ν(C=N+C=C) ν(C-H)aliph. ν(C-H)arom. δ(C-N)

L2

1745.74

1604.77*

(8.07)

3170.22

2981.95*

(5.93)

3031.92

2981.95*

(1.63)

1228.28

1273.02*

(-3.64)

(*) Experimental Frequency Error .

Table (10)

Comparison of experimental and theoretical electronic transition for ligands from CIS and

ZINDO calculation and Experiment method using Gaussian program.

Symbols Transition Experimental Theoretical

HL1

n→π

n→π*

n→π*

π→π*

328sh

287

240

222

CIS ZINDO

(222)max (311.59)max

L2

n→π*

π→π*

π→π*

297

243

-------

CIS ZINDO

(185)max (279.77)max

5. Conclusion In this paper, we succeeded to prepare mixed

ligands of (Quinoline-2–carboxylic acid and 4,4⁄-

dimethyl-2,2⁄-bipyridyl) with some heavy and light

transition metal ions. The new solid metal

complexes were isolated and characterized using

the available conventional techniques. The results

indicate that the primary ligand Quinoline-2–

carboxylic acid behaves as bidentate through the

nitrogen and oxygen atoms, while the co-ligand

4,4⁄ -dimethyl-2,2⁄-bipyridyl behaves as bidentate

ligand but through the two nitrogen atoms with

metal ions. Moreover, the results obtained for the

ligands and their complexes which were isolated in

solid state were compared with the results obtained

from the gas phase study using Hyper Chem-8 and

Gaussian programs exhibited almost identical

results between these states.

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Mukherjee, R.; Burman, A.C.; “Synthesis

and structure-activity relationships of potent

antitumor active quinoline and

naphthyridine derivatives.” Anticancer

Agents Med. Chem., 7(6):pp 685-709;

2007.

Journal of Al-Nahrain University Vol.18 (1), March, 2015, pp.28-38 Science

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الخلاصــة -2-تم تحضير معقدات جديدة من مفاعلة كوانلين

باي بريديال -'2,2داي مثيل,-'4,4حامض الكربوكسيلي و ، (II)النحاس ، II)نيكل )، (IIمع ايونات الفلزات:الكوبلت )

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